KR100822655B1 - 5-하이드록시트립타민-6 리간드로서의 1-아릴설포닐- 또는 1-알킬설포닐-헤테로사이클릴벤즈아졸, 이의 제조방법 및 이를 포함하는 약제학적 조성물 - Google Patents

5-하이드록시트립타민-6 리간드로서의 1-아릴설포닐- 또는 1-알킬설포닐-헤테로사이클릴벤즈아졸, 이의 제조방법 및 이를 포함하는 약제학적 조성물 Download PDF

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KR100822655B1
KR100822655B1 KR1020037006000A KR20037006000A KR100822655B1 KR 100822655 B1 KR100822655 B1 KR 100822655B1 KR 1020037006000 A KR1020037006000 A KR 1020037006000A KR 20037006000 A KR20037006000 A KR 20037006000A KR 100822655 B1 KR100822655 B1 KR 100822655B1
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alkyl
substituted
halogen
unsubstituted
piperazin
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KR1020037006000A
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KR20030040566A (ko
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켈리마이클제라드
콜데릭세실
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와이어쓰
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56Benzopyrazoles; Hydrogenated benzopyrazoles
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16Anti-Parkinson drugs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/18Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/22Anxiolytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/08Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Psychiatry (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Indole Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
KR1020037006000A 2000-11-02 2001-10-31 5-하이드록시트립타민-6 리간드로서의 1-아릴설포닐- 또는 1-알킬설포닐-헤테로사이클릴벤즈아졸, 이의 제조방법 및 이를 포함하는 약제학적 조성물 KR100822655B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US24511800P 2000-11-02 2000-11-02
US60/245,118 2000-11-02
PCT/US2001/045389 WO2002036562A2 (fr) 2000-11-02 2001-10-31 1-aryl- ou 1-alkylsulfonyl-heterocyclylbenzazoles en tant que ligands de 5-hydroxytryptamine-6

Publications (2)

Publication Number Publication Date
KR20030040566A KR20030040566A (ko) 2003-05-22
KR100822655B1 true KR100822655B1 (ko) 2008-04-17

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KR1020037006000A KR100822655B1 (ko) 2000-11-02 2001-10-31 5-하이드록시트립타민-6 리간드로서의 1-아릴설포닐- 또는 1-알킬설포닐-헤테로사이클릴벤즈아졸, 이의 제조방법 및 이를 포함하는 약제학적 조성물

Country Status (19)

Country Link
US (3) US20020115670A1 (fr)
EP (2) EP1343756A2 (fr)
JP (1) JP4184077B2 (fr)
KR (1) KR100822655B1 (fr)
CN (1) CN1222511C (fr)
AR (1) AR034270A1 (fr)
AU (2) AU2002220051B2 (fr)
BR (1) BR0115102B1 (fr)
CA (1) CA2426031C (fr)
EA (1) EA006205B1 (fr)
HU (1) HUP0303756A3 (fr)
IL (2) IL155443A0 (fr)
MX (1) MXPA03003800A (fr)
NO (1) NO326610B1 (fr)
NZ (1) NZ525592A (fr)
PL (1) PL213134B1 (fr)
TW (1) TWI282787B (fr)
WO (1) WO2002036562A2 (fr)
ZA (1) ZA200304188B (fr)

Families Citing this family (51)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL361887A1 (en) 2000-10-20 2004-10-04 Biovitrum Ab 2-, 3-, 4-, or 5-substituted-n1-(benzensulfonyl)indoles and their use in therapy
KR100600240B1 (ko) * 2001-06-07 2006-07-13 에프. 호프만-라 로슈 아게 5-ht6 수용체 친화도를 갖는 신규한 인돌 유도체
JP2005501019A (ja) * 2001-06-15 2005-01-13 エフ.ホフマン−ラ ロシュ アーゲー 5−ht6レセプター親和性を有する4−ピペラジニルインドール誘導体
CN1321110C (zh) * 2001-06-15 2007-06-13 弗·哈夫曼-拉罗切有限公司 具有5-ht6受体亲和力的4-哌嗪基吲哚衍生物
EP1408976B3 (fr) * 2001-07-20 2010-08-25 Psychogenics Inc. Traitement des troubles de deficit de l'attention/hyperactivite
GB0203811D0 (en) 2002-02-18 2002-04-03 Glaxo Group Ltd Compounds
PT1497266E (pt) 2002-03-27 2008-09-10 Glaxo Group Ltd Derivados de quinolina e sua utilização como ligandos 5-ht6
KR100657056B1 (ko) 2002-06-05 2006-12-13 에프. 호프만-라 로슈 아게 중추 신경계 장애의 치료를 위한 5-ht6-수용체조절제로서 1-설폰일-4-아미노알콕시 인돌 유도체
DE60322551D1 (de) 2002-09-17 2008-09-11 Hoffmann La Roche 2,4-substituierte indole und deren verwendung als 5-ht6 modulatoren
PL378120A1 (pl) * 2003-02-14 2006-03-06 Wyeth Heterocyklilo-3-sulfonyloindazole jako ligandy 5-hydroksytryptaminy
MXPA06000795A (es) 2003-07-22 2006-08-23 Arena Pharm Inc Derivados de diaril y arilheteroaril urea como moduladores del receptor 5-ht2a de serotonina utiles para la profilaxis y tratamiento de desordenes relacionados con el mismo.
SE0302760D0 (sv) * 2003-10-20 2003-10-20 Biovitrum Ab New compounds
NZ546887A (en) 2003-11-03 2009-04-30 Probiodrug Ag Combinations useful for the treatment of neuronal disorders
US7781478B2 (en) 2004-07-14 2010-08-24 Ptc Therapeutics, Inc. Methods for treating hepatitis C
BRPI0513713A (pt) 2004-07-28 2008-05-13 Glaxo Group Ltd derivados de piperazina úteis para o tratamento de distúrbios gastrointestinais
CA2619010C (fr) * 2005-08-15 2013-10-01 Wyeth Derives de 3-sulfonylindazole substitues en tant que ligands de 5-hydroxytryptamine-6
PE20071143A1 (es) * 2006-01-13 2008-01-20 Wyeth Corp Composicion farmaceutica que comprende un inhibidor de acetilcolinesterasa y un antagonista 5-hidroxitriptamina-6
WO2007098418A1 (fr) * 2006-02-17 2007-08-30 Memory Pharmaceuticals Corporation Composes ayant une affinite pour le recepteur 5-ht6
TW200808709A (en) 2006-03-31 2008-02-16 Glaxo Group Ltd Novel compounds
EP2001865A1 (fr) * 2006-04-05 2008-12-17 Wyeth a Corporation of the State of Delaware Dérivés de sulfonyl-3-hétérocyclylindazole utilisés en tant que ligands de la 5-hydroxytryptamine-6
WO2007120596A1 (fr) * 2006-04-12 2007-10-25 Wyeth DÉRIVÉS DE DIHYDRO[1,4]DIOXINO[2,3-e]INDAZOLE EN TANT QUE LIGANDS DE 5-HYDROXYTRYPTAMINE-6
DK2121602T3 (en) * 2007-01-08 2015-04-07 Suven Life Sciences Ltd 4- (Heterocyclyl) alkyl-N- (arylsulfonyl) -INDOLFORBINDELSER and their use as 5-HT 6 ligands
PL2114878T3 (pl) * 2007-01-08 2011-05-31 Suven Life Sciences Ltd Związki 5-(heterocyklilo)alkilo-N-(arylosulfonylo)indolowe i ich zastosowanie jako ligandy 5-HT6
AU2008216032A1 (en) * 2007-02-16 2008-08-21 Memory Pharmaceuticals Corporation 6 ' substituted indole and indazole derivatives having 5-HT6 receptor affinity
TW200848021A (en) 2007-03-06 2008-12-16 Wyeth Corp Sulfonylated heterocycles useful for modulation of the progesterone receptor
ATE513810T1 (de) 2007-05-03 2011-07-15 Suven Life Sciences Ltd Aminoalkoxy-aryl-sulfonamidverbindungen und ihre verwendung als 5-ht6-liganden
AU2008286760A1 (en) * 2007-08-15 2009-02-19 Memory Pharmaceuticals Corporation 3' substituted compounds having 5-HT6 receptor affinity
EP2508177A1 (fr) 2007-12-12 2012-10-10 Glaxo Group Limited Associations contenant de la 3-phenylsulfonyl-8-piperazinyl-1yl-quinoline
WO2009123714A2 (fr) 2008-04-02 2009-10-08 Arena Pharmaceuticals, Inc. Procédés de préparation de dérivés de pyrazole utiles comme modulateurs du récepteur de la sérotonine 5-ht<sb>2a</sb>
US20100016297A1 (en) * 2008-06-24 2010-01-21 Memory Pharmaceuticals Corporation Alkyl-substituted 3' compounds having 5-ht6 receptor affinity
US20100022581A1 (en) * 2008-07-02 2010-01-28 Memory Pharmaceuticals Corporation Pyrrolidine-substituted azaindole compounds having 5-ht6 receptor affinity
US20100029629A1 (en) * 2008-07-25 2010-02-04 Memory Pharmaceuticals Corporation Acyclic compounds having 5-ht6 receptor affinity
US20100056531A1 (en) * 2008-08-22 2010-03-04 Memory Pharmaceuticals Corporation Alkyl-substituted 3' compounds having 5-ht6 receptor affinity
WO2010032257A1 (fr) 2008-09-17 2010-03-25 Suven Life Sciences Limited Composés arylindolylsulfonamides et leur utilisation en tant que ligands de 5-ht<sb>6</sb>
ES2424036T3 (es) 2008-09-17 2013-09-26 Suven Life Sciences Limited Compuestos de amina de arilsulfonamida y su uso como ligandos de 5-HT6
WO2010062321A1 (fr) 2008-10-28 2010-06-03 Arena Pharmaceuticals, Inc. Procédés utiles pour la préparation de 1-[3-(4-bromo-2-méthyl-2h-pyrazol-3-yl)-4-méthoxy-phényl]-3-(2,4-difluoro‑phényl)-urée, et formes cristallines associées
UA100192C2 (en) * 2008-11-11 2012-11-26 УАЙТ ЭлЭлСи 1-(arylsulfonyl)-4-(piperazin-1-yl)-1h-benzimidazoles as 5-hydroxytryptamine-6 ligands
EP2424844A1 (fr) * 2009-04-30 2012-03-07 Abbott GmbH & Co. KG Composés de benzènesulfonanilide pour le traitement de troubles répondant à la modulation du récepteur 5-ht6 de la sérotonine
US8940716B2 (en) 2010-05-06 2015-01-27 Bristol-Myers Squibb Company Bicyclic heteroaryl compounds as GPR119 modulators
CA2799154A1 (fr) 2010-05-12 2011-11-17 Abbvie Inc. Inhibiteurs indazoliques des kinases
PL395469A1 (pl) 2011-06-29 2013-01-07 Adamed Spólka Z Ograniczona Odpowiedzialnoscia Pochodne indoloamin do leczenia chorób osrodkowego ukladu nerwowego
IN2013MU02611A (fr) 2013-08-07 2015-06-12 Cadila Healthcare Ltd
WO2015090233A1 (fr) 2013-12-20 2015-06-25 Sunshine Lake Pharma Co., Ltd. Composés hétérocycliques aromatiques et leur utilisation dans les produits pharmaceutiques
CN103880750A (zh) * 2014-03-18 2014-06-25 上海皓元生物医药科技有限公司 一种替格列汀关键中间体的制备方法
CN105541693B (zh) * 2014-07-08 2018-10-16 广东东阳光药业有限公司 芳杂环类衍生物及其在药物上的应用
US9550754B2 (en) * 2014-09-11 2017-01-24 AbbVie Deutschland GmbH & Co. KG 4,5-dihydropyrazole derivatives, pharmaceutical compositions containing them, and their use in therapy
CN107108556B (zh) * 2014-11-03 2020-09-29 艾欧米制药有限公司 药用化合物
EP4119141A1 (fr) 2015-06-12 2023-01-18 Axovant Sciences GmbH Nelotanserin pour la prophylaxie et le traitement d'un trouble du comportement en sommeil paradoxal
CA2992518A1 (fr) 2015-07-15 2017-01-19 Axovant Sciences Gmbh Derives d'arylheretoaryl uree en tant que modulateurs du recepteur serotoninergique 5-ht2a utiles pour la prophylaxie et le traitement d'hallucinations associees a une maladie neurodegenerative
JP7007374B2 (ja) * 2016-09-23 2022-01-24 ノバルティス アーゲー 腱及び/又は靭帯損傷に使用するためのインダゾール化合物
TWI748194B (zh) 2018-06-28 2021-12-01 德商菲尼克斯 Fxr有限責任公司 含有雙環核心部分之新穎lxr調節劑

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996003400A1 (fr) * 1994-07-26 1996-02-08 Pfizer Inc. Derives 4-indole utilises comme agonistes et antagonistes de la serotonine

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5849759A (en) * 1995-12-08 1998-12-15 Berlex Laboratories, Inc. Naphthyl-substituted benzimidazole derivatives as anti-coagulants
GB9716656D0 (en) * 1997-08-07 1997-10-15 Zeneca Ltd Chemical compounds
DK0930302T3 (da) * 1998-01-16 2003-07-21 Hoffmann La Roche Benzosulfonderivater
US6251893B1 (en) * 1998-06-15 2001-06-26 Nps Allelix Corp. Bicyclic piperidine and piperazine compounds having 5-HT6 receptor affinity
SE0002754D0 (sv) * 2000-07-21 2000-07-21 Pharmacia & Upjohn Ab New pharmaceutical combination formulation and method of treatment with the combination
PL361887A1 (en) * 2000-10-20 2004-10-04 Biovitrum Ab 2-, 3-, 4-, or 5-substituted-n1-(benzensulfonyl)indoles and their use in therapy

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996003400A1 (fr) * 1994-07-26 1996-02-08 Pfizer Inc. Derives 4-indole utilises comme agonistes et antagonistes de la serotonine

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Bioorg. Med. Chem. Lett. 10, pp.1719-1721, 2000

Also Published As

Publication number Publication date
EP1343756A2 (fr) 2003-09-17
AU2005102A (en) 2002-05-15
JP2004513111A (ja) 2004-04-30
PL213134B1 (pl) 2013-01-31
NO20031977L (no) 2003-06-30
EA200300528A1 (ru) 2003-10-30
HUP0303756A3 (en) 2009-08-28
US20040087595A1 (en) 2004-05-06
IL155443A0 (en) 2003-11-23
HUP0303756A2 (hu) 2004-03-01
AU2002220051B2 (en) 2007-05-24
IL155443A (en) 2011-06-30
EP2298738B1 (fr) 2012-09-19
EA006205B1 (ru) 2005-10-27
AR034270A1 (es) 2004-02-18
ZA200304188B (en) 2004-08-30
BR0115102A (pt) 2003-09-30
CN1484638A (zh) 2004-03-24
CA2426031A1 (fr) 2002-05-10
NO20031977D0 (no) 2003-04-30
EP2298738A1 (fr) 2011-03-23
US20020115670A1 (en) 2002-08-22
NZ525592A (en) 2004-07-30
CA2426031C (fr) 2011-10-04
TWI282787B (en) 2007-06-21
JP4184077B2 (ja) 2008-11-19
CN1222511C (zh) 2005-10-12
MXPA03003800A (es) 2003-08-20
WO2002036562A2 (fr) 2002-05-10
PL362138A1 (en) 2004-10-18
KR20030040566A (ko) 2003-05-22
US20040132741A1 (en) 2004-07-08
WO2002036562A3 (fr) 2003-01-23
BR0115102B1 (pt) 2013-11-26
NO326610B1 (no) 2009-01-19

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